jollybdap said:
The sticky issue is my tripod. I really like to capture some image at both ends of the day. But I don't see myself going back to hotel to pick up/drop off my tripod. It will more likely hang with me for the whole day. Do you have any good idea on how to do this?
I'd say that with modern DSLR with high usable ISO and stabilised lenses the need for a tripod goes away completely. I believe that these days tripods are special purpose tools useful in a few situations only - architecture photos with perspective correction using tilt/shift lenses, huge and heavy telephoto lenses, some macro work, product photos e.g food, special effects, etc. And you need a solid, often specialised tripod for that.
Compared with 100 ISO film in an SLR of the old days, today we can take useful photos with ISO 3200 (5 steps improvement) and IS (3 steps improvement). This is cumulative 8 shutter steps. In practical terms, with an IS lens you can shoot at 1/25 seconds or longer and have perfectly sharp photos. With ISO 3200 this allows you to take candle lit portraits with ease. So, try to say no to tripod. You will see that it really is easy.
It so happens that I now am traveling through Northern Italy. My experience is summarised below.
Keep things as simple and as light as possible. I believe that backpack is better than a shoulder bag, because it is more comfortable to wear for hours especially in hot weather. I use standard general purpose small 20 liter backpack and not a special photographic one. It is simple and more universal. In my backpack I carry: my 6D with 24-105 L IS, 70-300 L IS (on most days), water bottle, tiny umbrella, guide book and cut lunch. Polar filters in top backpack pocket. Camera with 24-105 in a ziplock plastic bag. The telephoto zoom in a ziplock plastic bag. No heavy protective cases. No hoods for the lenses. No shoulder strap. It all gets into way. The camera is either in the hand or in the backpack. This is all and it is sufficient. Many people will probably prefer a wide lens or wide zoom than a telephoto zoom, but I like capturing detail.
Even with this minimal gear you still stand out, as 95%+ of tourist take photos with their smart phones these days.
Italy is a wonderful country and certainly not more dangerous than most. Standard precautions still apply, as anywhere where you are a tourist and not a local.